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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by Jasper | July 14th, 2021
via: Unsplash / Mahkeo
If you’ve been looking for some fun questions to ask your boyfriend, this list has you covered! Whether you just started dating or you’re already celebrating anniversaries, pull out this list of questions to ask a guy to get to know him better!
These questions to ask your boyfriend are funny, deep, and thought-provoking! No more small talk about the football game - my fun questions to ask a guy will send the message that you really want to know him - for good and bad!
So, on your next date, order some appetizers, and dive in!
via: Unsplash / Alora Griffiths
No matter how long you’ve been dating, sometimes it can be a little hard to get a conversation started. These fun questions to ask your boyfriend are unique queries to ease any awkward silences. There is so much to learn about each other. Learn more through these fun questions that you may have never thought to ask!
Here are the 11 best fun questions to ask your boyfriend:
Good or bad, just the one that stands out the strongest.
Then do it!!
What made it such a momentous occasion?
Does he feel more inspired when he makes mistakes, or when he succeeds?
Maybe there are some family traditions he carries in his heart.
via: Unsplash / sept commercial
Solitaire? Doodle? Nap?
Is it an imaginary or real person? Living or passed? Why does he want to meet them?
How dedicated is he to achieving it? Commit to cheering him on!
More lottery tickets? A mansion? A private island, built for two????
Is it something others do intentionally or subconsciously?
via: Unsplash / Pawel Janiak
Is he a rocky road kind of guy? Or maybe strawberry cheesecake! There are almost as many options as there are people!
via: Unsplash / Cody Black
Everyone wants to be fully known and fully loved! Use these questions to ask a guy to get to know him better!
Make sure to thank him for his vulnerability, and keep his answers in confidence. You’re doing more than gathering random info here - you’re showing him your love and building trust.
Here are 13 questions to ask a guy to get to know your boyfriend:
Would there be one for different ages?
Maybe Parks and Recreation, or New Girl?
Would they talk about his silly antics or his feats of strength?
A specific characteristic, or a historic legacy?
It can be anywhere in the world, for any length of time.
via: Unsplash / Matt W Newman
Is he a lazy English bulldog or an energetic Great Dane? Maybe he is somewhere in between.
How long did it take, and was it worth it?
How does he feel know, and has he ever told them the truth?
What pushes him away?
Was there a magic moment, or did it happen over time? Did he tell anyone?
via: Unsplash / Scott Broome
Maybe a positive trigger and a negative one.
Was there one epic year he would love to experience again? Or one that was terrible and really needs a redo?
If not, what does he like?
via: Unsplash / Hean Prinsloo
Laughing together builds intimacy, so being silly is like vitamins for your relationship. These funny questions to ask a guy are great conversation starters to even more comical conversations!
Don't be afraid to let the questions get a little ridiculous. The more creative, the better! There are no wrong answers for most of these.
Here are 11 funny questions to ask a guy:
Like letting their nails grow too long or not brushing their teeth… yuck!
Find out all the details! Would he go alone? How long would he travel? Is there a time of year he would prefer?
How did people react??
Did he ever go back to pay for it?
Would he leave a map? Where would he put it?
via: Unsplash / N.
Who is his “Karen?”
Do you know anyone else with that crush?
Something sweet, smooth, and a little nutty? Pure vanilla? What flavor is he? Which would you pick?
Would he throw himself on your mercy, or come up with a grand excuse?
Mine was a glass decanter shaped like a pig. Can he beat that?
via: Unsplash / Sticker Mule
Take notes so that you never repeat it!
via: Unsplash / Toa Heftiba
Maybe you’re waiting in a long line, maybe you just want to try and connect in a new way. Try using some of these random questions to ask a guy to start some new discussions!
Here are 11 random questions to ask your boyfriend:
Maybe there are some new things he would like to try!
It’s ok if it’s physical, but a bonus if it’s not!
What makes up his dream girl?
A bus? His friend’s floor? How did he get into that situation?
Ideally both, but which one is more of a necessity?
via: Unsplash / Matthew Hamilton
Is he a practical person, or more sentimental?
Find out what his party skill is!
Maybe get him some tools so he can work towards this goal!
Is he self-reflective enough to know?
They’re good for you, but what does he think to taste wise?
via: Unsplash / Toa Heftiba
Does money burn through his pocket, or is he a scrooge?
via: Unsplash / Toa Heftiba
Chances are, your boyfriend has a complex mind. These interesting questions to ask a guy will open up his inner thoughts so that you can learn and love him in a whole new way!
Finding out more about his inner thoughts shows that you value all of who he is - not just his good looks! Break out these questions and get into the nitty-gritty!!
Here are 9 interesting questions to ask your boyfriend:
Show him you want to speak his language!
A cabin in the mountains, or a beachfront getaway?
Can people have more than one?
Is he a talker, or more of a doer?
Find out his relationship history.
via: Unsplash / Allef Vinicius
Maye it’s your sense of humor or your great taste in questions….
Is he a gift-giver? Complimenter? Grand gesture of love.
No questions asked! Ok, maybe a FEW questions.
And think of what you would call him!
via: Unsplash / Jacob Mejicanos
These questions are fun but intimate, so make sure you’re ready for them! I mean it, these deep questions to ask your boyfriend probably aren’t first-date appropriate, ok?
But, that doesn't mean these deep questions aren't important! If you guys are getting serious, you’ll be so glad you took the time to have these conversations.
Here are 13 deep questions to ask your boyfriend:
Is his happiness trending upward as your relationship goes on?
How will he know he has met them? Are they the same as yours?
Is he more nervous about positive or negative emotions?
Maybe he wants a big wedding, or to elope? Or maybe he pictures a life free of that commitment.
Does he want to be a millionaire by 30? Give 80% of his money away? Are you on the same page about your money philosophy?
via: Unsplash / Austin Distel
What does he imagine his ideal future family to look like?
Maybe try asking this one as “2 truths and a lie”!
Spiders? Death? Telemarketers? Maybe nothing at all!
Be ready to admit this yourself if he reciprocates!
Are there any deal breakers you should know about?
via: Unsplash / Şahin Yeşilyaprak
Is what you have a long term thing or just fun for now?
If not, what does he believe instead? What did his faith look like growing up?
Try and be open minded - we all make lots of mistakes when we’re young. But, pay attention too!
via: Unsplash / Dahiana Waszaj
Do you want some fun and sexy questions to ask your boyfriend? These questions will definitely get your boyfriend in a fun and sexy mood that he'll more than likely enjoy. He'll love answering these questions just as much as you enjoy asking him them.
Here are 9 fun sexy questions to ask your boyfriend:
Figure out what he loves on you and wear it whenever you feel like being a tease.
Talk about an awkward situation!
via: Pexels / Andrea Piacquadio
If he says yes, let him prove it to you.
And what would he want you to tattoo in that spot?
If he did, hopefully it was an exciting dream.
This question should give you an idea of what type of lingerie he's into.
Be prepared to control your jealousy with this question.
via: Pexels / mentatdgt
If he's clever, he'll ask you to kiss him so he can give you a precise answer.
Who would say no to this question?
via: Unsplash / Tyler Nix
Maybe you’ve read through this list, but feel even more lost than before?? No worries! This is an extensive list, meant to be spread out over many, many conversations.
I've got some basic tips to help you figure out exactly where to start with this fun list. So, read on, take some notes, and get ready to pick out a few awesome, fun questions.
Here is how to pick the best fun questions to ask your boyfriend:
via: Unsplash / Justin Follis
Before you even start, take some quick vitals on where your relationship is. Are you guys a new couple? Coming out of a rough patch? Starting to get serious? That information will help you choose appropriate questions for your boyfriend.
If you’re pretty new or experiencing a hard season, stick to lighter questions. Use funny questions to help ignite your spark and get you more connected. If you’re taking some next steps, use the deeper questions to make sure you’re solid and daydream together about your future.
via: Unsplash / Jonathan Borba
Pick the right questions for the right times. Have a long dinner ahead of you? Maybe pick out a few for the drive, a few for the appetizer and a few for dessert! Stuck in traffic? Break out some silly questions to ease the tension.
But, just like knowing the RIGHT time to pop some questions, be aware of the wrong times, too. Don’t get so excited about asking him some of these fun questions that it gets awkward or frustrating. If the game is on, or he just got home from work, wait ‘til later.
via: Unsplash / Radu Florin
Sometimes, you may hear an answer you weren’t expecting! While you’re allowed to feel all the things, try and stay neutral if you hear a surprising answer.
Prep yourself to be a good listener. Don’t ask a question you’re not ready for an honest answer for, and keep space open for communication. Remember, these fun questions are supposed to add fun and build love and intimacy - not break it!!
Here is a downloadable and printable List of fun questions to ask your boyfriend (right click the image and select Save Image As...)
There is so much laughter and connection waiting for you two as you plan out which of these fun questions to ask your boyfriend! And don’t stop here - I’m sure you can think of plenty of other questions to ask a guy that will help you grow even more in love.
These fun questions to ask a guy are sure to spice things up in the best way. For a date night in, or a special evening out, choose a few questions to ask your boyfriend and watch the sparks fly!
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